I don't know how to approach this. I can KIND OF speak to her in casual conversation, as I asked her about her leaving to join the military, and the three of us (her, me, and my sister) were all bullshitting in general, but I can't say anything that matters to her, such as "I like you" or "You're beautiful" or even something as silly as "What kind of movies do you like?". I'm trying to be intelligent about why I can't just ask her out or something, but it defaults to a simple reason. Not shyness or self esteem...entirely. Hell even rejection isn't that horrifying.

What if she says yes to a date and I screw it up, or we just don't click, or something equally horrible? I can deal with being shut down, anger and rage are sort of bedfellows in my life. But embarassment, incompetence, worst of all the thought of blowing my only shot with her...it is making me feel queezy just typing it here. I know if I said hey, lets go see a movie when you come back, she'd say sure. But I desperately don't want it to fail, enough so that I'll let this feeling of desire linger til I'm more confident with myself and what I can offer as a guy.

Dice, you're a girl (most of the time), would something like this make you feel awkward, being the subject of one's infatuation?

I don't know how to approach this. I can KIND OF speak to her in casual conversation, as I asked her about her leaving to join the military, and the three of us (her, me, and my sister) were all bullshitting in general, but I can't say anything that matters to her, such as "I like you" or "You're beautiful" or even something as silly as "What kind of movies do you like?". I'm trying to be intelligent about why I can't just ask her out or something, but it defaults to a simple reason. Not shyness or self esteem...entirely. Hell even rejection isn't that horrifying.

Bullshitting is great, keep up with that, I'm sure a lot of relationships have started through just goofing around. Saying "I like you" and "your beautiful" though?? No. No, no, them words are off-limits until you know for FACT there is a spark. Saying that otherwise can send her for the hills or worse, make it too easy for her and she's out, she knows she has you hook, line, and sinker. Rejection happens, it's a fact. I've been rejected plenty. It happens, it hurts, you get up and -gracefully- move on.

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What if she says yes to a date and I screw it up, or we just don't click, or something equally horrible? I can deal with being shut down, anger and rage are sort of bedfellows in my life. But embarassment, incompetence, worst of all the thought of blowing my only shot with her...it is making me feel queezy just typing it here. I know if I said hey, lets go see a movie when you come back, she'd say sure. But I desperately don't want it to fail, enough so that I'll let this feeling of desire linger til I'm more confident with myself and what I can offer as a guy.

Nothing will stop you more than being shy/timid/nervous etc. If there's a click, first date awkwardness won't even be a thang, likely she'd have it too, then you look passed it because you still had an "ok" time and wait for the second date where you're both that much less nervous but both agreed for a second date. Boyfriend and I had a really awkward first date, barely said anything at all (seeing a movie together helped, you don't have to talk much aside from goofy commentary during it. Four years later, we're best buds, and talk about any/everything.

Also to, keep in mind it is your sister's BFFF. This might be awkward for your sister, not just for you. What's it like for your sister to welcome her friend into the house only for her to be seeing you instead? You gotta approach this gently, a day at a time, but remember -- if it was meant to happen, it will.

There is the one issue of her leaving for military basic training today or tomorrow, forget which. She probably won't be back here til.....fuck I dunno when. My sister's not even remotely disconcerted by the idea of me trying to hook up with her (mostly because she knows that I'm a chickenshit who won't work the nerve up). I think she'd be happy with the idea because she knows I'm far less stupid and more caring and considerate then most of the guys they know.

I haven't been this distracted by a lady since I was in grade school...I forgot how much this feeling sucks. But damn she's beautiful.

There is the one issue of her leaving for military basic training today or tomorrow, forget which. She probably won't be back here til.....fuck I dunno when. My sister's not even remotely disconcerted by the idea of me trying to hook up with her (mostly because she knows that I'm a chickenshit who won't work the nerve up). I think she'd be happy with the idea because she knows I'm far less stupid and more caring and considerate then most of the guys they know.

I haven't been this distracted by a lady since I was in grade school...I forgot how much this feeling sucks. But damn she's beautiful.

well.... this is probably horrible advice.... but hot damn man, you must act fast!! or at least I would.... it would bother the piss out of me if she left and I didn't at least express myself.....

but I wouldn't want to make things too over the top considering she is leaving and probably more concerned about that than anything else and you don't won't to come off as insensitive by over-complicating things for her ATM..... Soooo... I would probably go about it like this.... I would use her leaving as a segway into the expression of my feelings... something to the the effect of "hey, you know what? I got to thinking about your going away and all and it really made me realize just how much I think you freakin' rock! I just needed you to know that." then I would proceed to honestly express what you have already said here..... continuing with (after a brief chuckle at myself for beginning to spill the beans) "no seriously though, I haven't been so impressed by a female since detention, being grounded and homework were the banes of my existence."...... now here is the key to the whole plan... ready???..... you immediately move into a new (prepared) topic you can easily bullshit with her about. This is super-important. See, you've delivered a message that can cultivate in her mind, the impact of which can lead to a very awkward moment if given the opportunity.... however if you immediately move into something to get her train of thought of the gravity of what you've said into something positive and engaging you accomplish a number of things.... the most important of which is the reduction of a chance of rejection because you haven't actually provided her the opportunity yet to reject you....

voooo-waaaahhh-lahhhh!! message delivered, you feel better, she'll be off at boot camp dreaming about your hot ass because you left her with the notion that you'll be doing the same.... she gets back, you live happily ever after....

..... in all honesty though, this is really what I would do.... I've never been rejected when I've just been honest, down to earth in my delivery and somewhat strategic about the follow up convo... though I do have a tendency to be blunt and open to a fault which I know has made for some uncomfortable moments, I can't recall any really turning out badly.... the only time things have fallen to pieces in my efforts to express such affections in the past is when I make things SEEM WAAAAAY MORE SERIOUS then in fact they are.... I mean, think about it... your clearly not a freakin' unintelligable cave troll and all your doing is expressing to her that you feel she is superior to other females in your eyes... there is NO reason that any female would recieve that negatively unless it was accompanied with a thick slab of "creepy-weirdo-semi-obsessive-ness".

EDIT: Objectively speaking, I would take any advice Dice offers long before mine by the way.... I really never know what the hell I'm doing in life, but I just thought I'd offer you how I would go about it. Good luck friend!